I really enjoy the rare moments I get to have a cigar and a glass of bourbon after a long week, either on my own or with friends.

Most of us are too busy – so taking the time to slow down, indulge the palette, and have good conversation is a true pleasure.

I know there are a few EG readers who enjoy the same ritual, and a handful of others who are curious about cigars. So I’m happy to make this updated resource available for the next time you enjoy you a cigar.

There may come a time when someone offers you a cigar to share in a celebration. The classic examples are the birth of a child, getting a new job, or buying a new home.

If you don’t smoke, politely decline. If you do – even just casually – accept the gesture and enthusiastically take part in the celebration. It’s something truly special.

But the last thing you want to do when sharing a cigar with friends or family is to look like an idiot. What if you’ve never been comfortable with the art of cigar smoking? What if it’s totally new to you?

That’s just why we’ve got this resource for you. From the history of cigars, to how to choose your first cigar, to tips for purchasing a humidor… you’ll find answers to all your burning questions.

Famous Cigar Smokers of the Last Century

First, some perspective. History is filled with examples of great men who smoked cigars. You may want to emulate these guys beyond just their cigar habits.

Sir Winston Churchill

Perhaps the most famous statesman of all time. Churchill was elected British Prime Minister at the height of World War II and promptly united a divided Europe in its battle against Nazi Germany. And he knew his cigars, becoming famous for flashing the “V” for victory sign with one hand while holding a fine La Aroma de Cuba in the other.

La Aroma de Cuba Price: La Aroma de Cuba

Red Auerbach

Legendary coach of the NBA’s Boston Celtics. He enjoyed a cigar after every Celtics victory that he coached – over 900 in total. He was tough and knew the power of teamwork and camaraderie. Red’s favorite cigar was the Nicaraguan Hoyo de Monterrey Excalibur.

Hoyo de Monterrey Excalibur Price: Hoyo de Monterrey Excalibur

Jack Nicholson

A Hollywood legend, Nicholson is famous for loving both cigars and the Los Angeles Lakers. Even though non-smoking laws have altered his public smoking habits at games, he has been known to sneak into the men’s room at Lakers games to enjoy a classic Montecristo No. 2.

Montecristo No. 2 Price: Montecristo No. 2

Bill Clinton

The charismatic 42nd President of the United States enjoyed a good cigar when the time was right —like after a hard fought political battle against Newt Gingrich or a winning putt on the golf course.

Gurkha Grand Reserve Price: Gurkha Grand Reserve

Whether you’re as experienced as these men or totally new to the world of cigars, here are some tips that you should keep in mind.

Choosing the Right Cigar For Your First Time

If you delight in your senses, you may well become a connoisseur of cigars. But a lot depends on your very first stogie.

If you’re offered one by a friend, by all means, accept it. But when you’re picking out your first cigar, keep these general rules in mind.


You probably should look to spend around $5-$8 on your first stogie. You can get a very good cigar for this price. And if you don’t like it for some reason, you’re only out a few bucks and it’s not a big deal.

Body, Strength, and Flavor

In general, you should start off with a mild cigar with light body, strength, and flavor. There will be many options for mild cigars in the $5-$8 range.

Look for one described as an all-around stick for everyone. You want something that won’t be too heavy but still has enough complexity for guys who tend to prefer medium or full bodied smokes.

Of course, you don’t have to stick with a mild cigar. If you enjoy strong coffee or you are an ex-cigarette smoker, you would probably be just fine with a medium-bodied or even a full-bodied cigar.

Where to Buy

Your best bet is a brick and mortar cigar shop. That’s because you can get the help of a real tobacconist who knows the cigars they sell and can make an ideal recommendation.

Online stores are great. And you may be able to find better deals online. But the first time around, getting the help of an expert in the shop is a smart idea.

Whatever you do, do not buy your first (or any subsequent) cigar at a gas station or convenience store. They’re cheap, they’re not properly stored in a humidor, and you will almost certainly wind up regretting your purchase.

5 Options for New Cigar Smokers

Avo Classic

Avo is one of the best-known cigar brands in the world, created by pianist Avo Uvezian after he went into the cigar business.

Avo Classic cigars are mild, creamy blends in Connecticut wrappers. While they are not the most complex sticks out there, they offer a consistent, enjoyable, and relaxing experience and are perfect for a novice in search of something mild.

Avo Classic Price: Avo Classic

CAO Gold Vintage

CAO Gold Vintage cigars are enclosed in Ecuadorian Connecticut wrappers grown in 2004, a particularly good year (I wonder how they manage to keep producing cigars with this wrapper though), with a combination of Cuban-seed Honduran and Nicaraguan tobacco inside.

This cigar offers a smooth, creamy, mild flavor with subtle nutty flavors. The blend takes on a medium-bodied character as you progress. If you cannot decide between a mild- or medium-bodied cigar for your first smoke, this is a perfect choice.

CAO Gold Vintage Price: CAO Gold Vintage

Ashton Aged Maduro

Ashton cigars are acclaimed globally for their high level of quality. The Ashton Aged Maduro offers a good starting point for a beginner who is open to a full-bodied experience and wants to try a good maduro (a cigar with a dark, maduro wrapper leaf).

Consistent spice, coffee flavors, and notes of leather, nuts, and lime create a complex and enjoyable blend.

Ashton Aged Maduro Price: Ashton Aged Maduro

Rocky Patel Edge Lite

Rocky Patel is a boutique cigar manufacturer who has risen to prominence in the premium cigar world despite the odds, and it’s thanks largely to amazing blends like this one.

The Rocky Patel Edge Lite is a medium- to full-bodied cigar with a rich, creamy flavor and an excellent draw and burn.

And it only costs $5, which makes it a great choice for a cigar newbie.

Rocky Patel Edge Light Price: Rocky Patel Edge Light

Oliva Connecticut Reserve & Oliva Serie G

Oliva is best known for manufacturing delicious full-bodied cigars. The Serie G Maduro is a great example, with a dark oily wrapper and amazingly rich chocolate and coffee flavors against a backdrop of toasted nuts.

If you’re interested in Oliva but prefer to try something milder, the Connecticut Reserve is a light-to-medium bodied cigar with flavors of butter and toasted almonds. Thanks to those flavorful and aromatic touches, it’s a milder smoke without ever being dull or unmemorable.

Oliva Connecticut Reserve Price: Oliva Connecticut Reserve

Oliva Serie G Price: Oliva Serie G

For International Readers: Partagas Shorts

Have access to Cubans and looking for an affordable cigar that can deliver an awesome experience? The Partagas Shorts cost $6-$8 for a stick (you might need to add 2x that amount for taxes though, depending on where you live) and offers great construction.

You also get a delicious blend of flavors: sweet latte combined with chocolate, vanilla, honey, wood, and spice.

Honorable Mentions

Enjoy your first cigar, but don’t forget to pick up several and give it at least a few tries if you don’t like your first one. Many smokers find their first attempt with a cigar a bit awkward, but enjoy their second and third much more.

Cutting the Cigar

This is something all men who smoke cigars should know how to do.  It does not involve:

  • scissors
  • Swiss Army knife knock-offs
  • your own teeth

Especially not your teeth!

In most cases, the best cutting option is straight cut. Use a single bladed cigar cutter to chop off the head in one motion and leave the wrapper intact.

Stackhouse Guillotine Cutter Price: Stackhouse Guillotine Cutter

Cut the cap on the ‘head’ (that’s the end you smoke — the end you light is called the ‘foot’) to create enough of an opening to smoke it comfortably while not distorting the shape of the cigar.

Lighting the Cigar

Go with a butane torch lighter. It might not look as cool as when guys in the movies use a match. But it’s the best bet, especially for beginners.

Vertigo Excalibur Lighter Price: Vertigo Excalibur Lighter

Avoid cigarette lighters. The cigar can take on the taste of the lighter fluid, mucking up the flavor of your cherished first smoke.

Smoking the Cigar

A cigar is so much more than a simple cigarette. Smoking one is not about getting a tobacco fix. This is a way to enjoy the company of friends and relax.

Hold the smoke in your mouth, enjoy it, and then blow it out. While smoking, slowly rotate the cigar to get an even burn.

Experienced smokers: Do not take a drag off it like you would a cigarette – and do not inhale. If you inhale, you run the risk of coughing out a lung or blowing chunks.

As for basic cigar smoking etiquette…

  • Don’t light up your cigar with someone else’s.
  • Cigars are not supposed to be shared. Don’t ask your friend to try a puff of his cigar.
  • Never blow cigar smoke in someone’s face.
  • Cigar smoke can be unpleasant for non-smokers — always make sure the people around you are comfortable with the smoke.
  • Don’t stub your cigar out like you would a cigarette when you’re done. Just lay it down in the ashtray and allow it to go out on its own.
  • While it’s up for debate, etiquette dictates removing the band when you start smoking. Since this general rule is very rarely followed, it’s really up to you if you want to leave it on.

Where Should I Store My Cigars? Do I Need a Humidor?

Let’s say you’ve tried a few of the recommendations above. You have an idea of what you like, so you want to buy several and keep them at home for special occasions. Where should you store them?

First off, how many cigars do you have? If you still don’t have a big collection, you may not need a humidor yet. Some handy household supplies – like zip lock bags – will do for now.

You can also make your own makeshift humidor from a cooler – a coolidor. It’s a lot better than just a plastic bag – but still not going to do as good a job as a true humidor.

What Is a Humidor?

A humidor is a specially designed storage container for cigars. It preserves the careful combination of temperature and moisture that will keep a cigar in ideal condition. It’s not a totally sealed environment since that could cause molding. Instead it allows air to circulate while still keeping your cigars at their best.

Most experts recommend Spanish Cedar for the interior lining of humidors. This type of wood is both beautiful and functional. It can withstand humidity without warping or distorting over time – unlike many other types of wood.

Whitetail Glasstop Humidor Price: Whitetail Glasstop Humidor

Humidors come in all sizes – from personal and portable devices to room-sized walk-in humidors. If you’re new to cigar collecting and just want to make sure your stogies stay in ideal condition, a personal humidor is fine. These small, relatively lightweight models can hold dozens of cigars and aren’t prohibitively expensive.

What Size Humidor Should I Get?

How many boxes of cigars do you think you’ll have around at a given time? Consider that a box may hold up to 25 cigars. Use that as a guide to calculate how much space you’ll need.

Buying a humidor slightly larger than what you think you’ll need is a good plan. That gives you more flexibility without wasting space — so you can expand your collection without instantly outgrowing your humidor.

Whitetail II Glasstop Humidor Price: Whitetail II Glasstop Humidor

Setting Up Your Humidor

You’ll need a thermometer to put inside your humidor, as well as a digital hygrometer — that’s an instrument that measures humidity. That way you always know if your humidor is working at its ideal settings. Try to keep the humidity between 68% and 72% and temperature at about 65-70° F.

To get your humidor up and running, you’ll need to complete a few steps.

  1. Prepare your humidifier. It’s the device inside the humidor that keeps the interior humidity level stable. Depending on your specific model, you’ll probably need to fill it with distilled water or propylene glycol. Make sure to follow the instructions.
  2. Wipe down the inside and let it dry. Use distilled water and wait until it’s totally dry, usually about an hour.
  3. Place a small glass of distilled water inside the humidor. Put your hygrometer and thermometer in there as well.
  4. Wait 48 hours. Keep an eye on the glass so it never goes totally empty. Add more as the interior walls of the humidor absorb the water.

You’re all set! Watch the humidity level for a few days to make sure it’s stable.

For longer-term humidification, you’ll need these little jars of activator beads; just add water and the beads will slowly release moisture as needed to maintain that 65-70% humidity!

Enjoy the Hobby

If you have trouble getting the settings just right, give it some time and experimentation. This is a hobby – so enjoy the process! There are lots of different humidors out there and theories of how to season them.

As for the cigars themselves, have fun with the process of trying new smokes. Get together with the guys to discover some new favorites. Visit different tobacco shops in your area to get tips from local pros. There’s always something new to learn – these are just the basics!

Any other recommendations – for first time cigar picks, tips on enjoying that first smoke without looking a fool, or anything else? Let us know in the comments.

Got a question? Hit me up!

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